Softening agent



Patented Oct. 29, 1946 helm, Germany;

C stodian V 3 Claims.

The present invention relates to valuable softening agents more particularly to those of the general formula:

H2C-CH1 H2CCH1 tov a Ma m V. wherein R stands for a member of the group consisting of a methine radical and the methine radical forming a part ofa c yclohexane ringz and R1 stands for a radical selected frp rnthe aliphatic and benzene series the essential; characteristic of the methine radical being the existenceoi three linkages. each of whichis satisfied by other separate alkylene or arylenesub'stituentsr V The'new softening agents, are obta ned by condensing two molecular" proportionsof iuriural with one molecular proportion of an aliphatic or cycloaliphatic ketone containi ng reactive alkyl groups, entirely hydrogenating the formed condensation products and esterifying the secondary alcohols thus obtained b y means of carboxylic acids of the aliphatic and benzene series or-their reactive derivatives.

The present new ester compounds exhibit an excellent softening effect on the various thermoplastic compounds of a highamolecularl weight and the artificial masses-obtained therewith, such as highly polymerised vinyl compounds, polyacrylic acid esters and mixed polymerisation products therefrom, moreover cellulosicderivatives. i In order to vention the following examples are given, the parts being by weight 1 and all temperatures in degrees centigrade. I

7 Example! furyl-3- hydroxypentane" and 6.6 parts oi a'cetic' vested in the Alien Pi-operty 1:

furtherillustrate present incondenser.

Nonr'awiiig; App cation February 6;"1941, Serial No. 377,711. InG'ermanTFebruary 8,1940- H: g:

1 r F xi wd- .J. i passes over at 1.5 mms. pressure at 180 to 8 ssay colorless a d t do les l." whi hci sn miscible with iivatert H I --Corresp ondin g products are obtained when re- 5, placing the acetic acid; by other aliphaticjacids such as. caproic; caprylic or capric acid A mixture of 228 zpartsrof the alcohol used in Example, 1 and 250 parts of benzoic acid anhydride is siowiyji f ated t 2oofito 220, the esteri'fication has been fihished. the eact n product is digested with afdilute sodium carbi solution-in order to 'r'emove the formed 10 boils at 1 5iessj i'reatf2oo to 21p sayi cqu s,

30 *Crrespo'nding estersare obtained'wh'eri steifif fying with derivatives of benzoic acidbei'ngfs bi ll e h i l 19 ped: a?

r i mamas 4 50 partsjoithealcohol as isd Legfcregoin'i ex" mp1es re'lmiie'd with 10 "parts gof a fmix iulfe er'ai-boiiyiic acids of'ac'id mining; 324-, ohflaih'able by oxidising the higher aicohbisiwhich are wen known lay-products of the methanol synthesis. 1 53 1 ss v v-hcaie 2 9 to 2 0 While introducing nitrogen into the reaction vve'ssel. ith the nitrogen" which passesthrough also waterisrernovd 7 The same estefisobtain accordingito the following method: A mixture of equal quantities of the alcohol and the aforesaid mixturerof carboxylic acids- -is" subiected'lin the-1 presence of toluene as assistant liquor and a small amount of benzene sulfonic acid to the aceotropic distillation. ,When the splitting off of water has been finished the reaction product is isolated'as described in' Exa'mple 2.

ifi eic meadmix iire esiarsyb s. l pr ssu e ammo 240?. -asa1c lq 0d 5?? less 011. s

boils at223 to 226 at 0.7 mm.

Example 4 When esterifying by means of adipic acid the formed diester of the formula:

is an odourless oil boiling above swat 151mm.

pressure.

Instead of adipic acid other dicarboxylic acids such as succinic acid may be used as esterifying agent. I V

In the manner as described in the foregoing examples other entirely hydrogenated condensation products of furfural with suitable ketones such as methylethylketone, diethyl-ketone, cyclohexanone and its alkylated derivatives suchas isooctylcyclohexanone yield valuable products by esterification.

Avmixture of 246.parts of 1.5-ditetrahydrofur yl-3-hydroxypentane and 116 parts of isoheptoxyacetic acid is heated for about 6 hours at about 140 in,a vacuo of 20 to 25 mm. pressure, the-formed water distilling 011. Then the temperature is increased during about Ghours to 180 and the reaction mixture is held at this temperature for 12 hours. The formed ester is isolated by fractionating distillation. The yield is nearly theoretical. The ester thus obtained of the formula:

HaC-CH: H2C-CHI H20 n-cmom-cH-cmom-no H: I I o a 0 CH:Q-C 1111:

g Example 6 A mixture of 246 parts of 'LS-ditetrahydrofuryl-3-hydroxypentane and 152 parts of phenoxyacetic acid is heated at reduced pressure. With an almost theoretical yield by fractional distillation the formed ester of the formula:

mc----- cn, M v iHl 'CH2 H, cn-cmom-on-omonrnc on, i'

is obtained as a colorless and odourlesso'il, which pressure and-is not miscible with water.

4 A similar ester is obtained when using the phenoxy Propionic acid as esterifying agent.

Example 7 By condensing the alkali metal compound of glycolmonobutylether with the sodium salt of monochloroacetic acid there is obtained the dietheracetic acid of the formula:

CHr-O-CHz-COOH 'boiling'at 15 mm. pressure at 163 to 165.

176 parts of thisacid are mixed with 246 parts of 1:5-ditetrahydrofuryl-3-hydroxypentane and the mixture is heated at reduced pressure. With .an almost theoretical yield the ester of the for- I a, (5H:

l O-CHrCHr-O-CHn-CHFCHz-CH:

is obtained as a colorless and odourless oil, which is not miscible with water and boils at 0.5 mm. pressure at 215 to 220.

The ethercarboxylic acid derived from glycolmonophenylether yields an ester of similar properties. I

, Example 8 300 parts of 2.6-di-trahydr0furfurylmethyl-cyclohexanol obtainable by hydrogenating the yellow condensation product of two molecular proportions of furfural and one molecular proportion of cyclohexanone are mixed with 400 parts of acetic acid anhydride and the mixture is heated under reflux for about 3 hours. By a fractionating distillation with an almost theoretical yield the formed ester of the formula; Y

being a colorless and odourless oil, which boils at 223 to 226 at 0.7 mm. pressure and is not miscible with water, and exhibits an excellent softening efiect on thermoplastic compounds of high molecular weight and cellulose derivatives.

2.- A softening agent of the formula:

5 6 being a colorless and odourless oil, which boils at 3. Softening agents or the general formula 210 to 215 at 1 mm. pressure and is not miscible with water, and exhibits an excellent softening effect on thermoplastic compounds of high mo- H CHPCHPCH CHPCHPH lecular weight and cellulose derivatives. 5 0 

